Cuba Yacht Charter

Regardless of whether you fly directly into Cuba, or board your vessel in Florida and transit the 85 nautical miles across the Gulf Stream through the Florida Straits, Havana is the perfect place to start. You can easily spend 2-3 days exploring this multi-faceted city, and only scratch the surface. It’s your choice: explore the city? Or explore the coast?

DAY 1: Arrival in Key West

The crew will fetch you at the airport and bring you to your yacht in old Key West, just off Duval Street. This is a great primer for your trip, because it's tropical, laid back and there's fun in the air.

After you get your gear stowed onboard, you might walk around town – and don't forget to tour the Hemingway House. This is where the adventure begins. Hemingway loved Cuba, and you will be in Papa's Finca Vigia, just outside Havana soon enough.

DAY 2: Old Havana

You'll hear the main engines rumbling awake at dawn. Another choice – sleep in and enjoy the yacht's slow motion, or have coffee on the top deck as daybreak illuminates the port of Key West on your way south to the Gulf Stream and international waters.

At Marina Hemingway, you'll clear customs into the Republic of Cuba. You can take a ride into the city and have lunch at a rooftop 'palador' private restaurant overlooking Old Havana, or visit with local artists and stroll the 'Malecon.'

DAY 3: More of the Historic City

Discover a different perspective of Havana's best neighborhoods and former seaside beaches and clubs. After cruising along the 'Malecon' sea wall, the harbor entrance is dwarfed by the imposing fortress guarding the entrance to Havana Bay.

From Marina Hemingway, vintage 50's convertibles will whisk you away for a top-down tour of the city, including stops at the Hemingway Museum Finca Vigia, where his beloved fishing boat 'PILAR' is on display.

DAY 4: Cruise to Varadero

Head east to Varadero, a roughly 85-mile cruise. Take-in the hilly coastline and do a loop through the Port of Matanzas, which you can visit once you're checked in at the Varadero Marlin Marina.

You could also enjoy cocktails on the rooftop bar of the Dupont Family Mansion, XANADU, overlooking the pristine beach and the golf course.

DAY 5: Continue Enjoying Varadero

Your Cuban dive-master and guide will introduce you to the most unspoiled reefs in the world and put you on some of the best fishing in the Caribbean.

For those who haven't had enough culture, there are art studios in Matanzas that are a must-see. You can meet the artists and discuss symbolism, politics and, in some cases, the rage that appears in their work.

DAY 6: Explore the Cays

Cruise to local cays and explore the coastal bays, or head inland to visit a tobacco farm and see Cuban cigars being made. Meet some farmers and enjoy a meal at a countryside home. Alternatively, you might want to hit Havana again on your way back to Key West.

DAY 7: Return to Key West

Relax on the passage back to Key West, and start planning your next cruise to the South Coast of Cuba, starting in Cienfuegos.